Aspergillosis refers to an infection with any species from the genus Aspergillus. Pleural aspergillosis is an uncommon disease with less than 30 cases having been reported in the literature since 1958. The etiologic factors for this aspergillosis are preexisting pulmonary tuberculosis, bronchopleural fistula, pleural drainage, and a lung resection. Surgical removal of the aspergillus-infected pleura is the main treatment for managing this disease. We have experienced two cases of pleural aspergillosis as a complication of a preexisting chronic empyema. The chest radiographs showed a pyopneumothorax with cavitation and the chest computed tomographic scans revealed a loculated pyopneumothorax with cavity formation suggesting a bronchopleural fistula. A grossly purulent fluid was extracted by thoracentesis, and Aspergillus fumigatus was grown from a fungus culture of the fluid. A decortication, wedge resection with a pleurectomy and a pleuropneumonectomy were performed. The postoperative course was satisfactory and the patients have been in good condition up to now. Pleural aspergillosis is a very rare and potentially life-threatening disease. However, good result without significant complication were obtained by treatment with systemic antifungal agents and surgical removal.